The good people at Brain Pickings have unearthed some keys to aid listening to music, taken from a book published 30 years ago by composer Elliott Schwartz.
They're all pretty interesting and useful. In the last few years I'd done a couple of them without realizing they were in Mr. Schwartz's book and I had noticed myself appreciating different things about the music I listed to -- and not just the classical music he references, either. When you realize you can actually tell by the tone of the voice that a singer is smiling during a certain part of the song, it's not just because the singer is that good at communicating -- although she is. It's because you've learned to listen more closely instead of just having the music as background while you do something else.
Even at less involved levels of listening most folks realize this. If we want an exercise soundtrack, it doesn't matter whether we're James Taylor fans or not -- we're not picking him for that playlist. Taylor may best Billy Idol in songwriting craftsmanship and a hundred other areas (I don't personally think he does, but then I don't much care for Taylor so you shouldn't go by me). But when I am flagging in my last five minutes on the elliptical machine, "Rebel Yell" will get me across the finish line in a way that "Fire and Rain" cannot manage.
The most interesting thing to me was that Mr. Schwartz said that folks in 1982 needed the keys he discusses, because our appreciative ear and faculties had been “dulled by our built-in twentieth-century habit of tuning out.” If I'm any indication, thirty years on we haven't gotten much better at breaking that habit.
(ETA omitted link to the singer in the second paragraph)